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Competitive Reaction of –OH and –NH2 Functional Groups on Synthesis of Bioactive ortho-Cetamol Derivative (4-Allyl-2-methoxy-N-acetyl-o-amino phenol) from Amino-Eugenol
Corresponding Author(s) : I.M. Sudarma
Asian Journal of Chemistry,
Vol. 27 No. 10 (2015): Vol 27 Issue 10
Abstract
The main aim of this research was to develop new or novel compounds with potential biological activity from readily accessed natural products, in particular eugenol (1). A new ortho-cetamol derivative (4-allyl-2-methoxy-N-acetyl-o-amino phenol) was synthesized from amino-eugenol which was prepared by series reactions from eugenol (4-allyl-2-methoxy-phenol). Eugenol has been transformed to its nitro eugenol (2) in good yield by adding potassium hydrogen sulfate and ammonium nitrate. The nitro group of eugenol reduced smoothly to amino-eugenol (3) by treating with zinc and formic acid. Reaction of amino eugenol with acetyl chloride in the presence of sodium carbonate produced 2-acetato-5-allyl-3-methoxy-aniline (4) (16.16 %) and 4-allyl-2-methoxy-N-acetyl-o-aminophenol (5) (58.58 %) and competitive reaction occured between –OH and –NH2 groups of amino-eugenol during the acylation reaction due to steric hindrance.
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- S.A. Burt and R.D. Reinders, Lett. Appl. Microbiol., 36, 162 (2003); doi:10.1046/j.1472-765X.2003.01285.x.
- S.I. Kim, J.H. Yi, J.- Tak and Y.-J. Ahn, Vet. Parasitol., 120, 297 (2004); doi:10.1016/j.vetpar.2003.12.016.
- Y. Li, C. Xu, Q. Zhang, J.Y. Liu and R.X. Tan, J. Ethnopharmacol., 98, 329 (2005); doi:10.1016/j.jep.2005.01.020.
- M. Pisano, G. Pagnan, M. Loi, M.E. Mura, M.G. Tilocca, G. Palmieri, D. Fabbri, M.A. Dettori, G. Delogu, M. Ponzoni and C. Rozzo, Mol. Cancer, 6, 8 (2007); doi:10.1186/1476-4598-6-8.
- R. Gao, S. Zhou, P. Zhou and Y. Feng, Asian J. Chem., 26, S173 (2014); doi:10.14233/ajchem.2014.19039.
- T. Sumana, P. Iyengar, C. Sanjeevarayappa, K.E. Manoj Kumar and K. Vijay, J. Appl. Chem., 3, 47 (2014).
- S.S. Praveen Kumar Darsi, K.S. Nagamani, B. Rama Devi, A. Naidu and P.K. Dubey, Der Pharma Chemica, 3, 35 (2011).
- B. Baghernejad, M.M. Heravi, H.A. Oskooie, Y.S. Beheshtiha, G.U. J. Sci., 22, 169 (2009).
- D. Gowda, B. Mahesh and G. Shankare, Indian J. Chem., 40B, 75 (2001).
- I.M. Sudarma, N. Wazni, N. Wildawaty, E. Yuanita and I.W. Suana, Asian. J. Chem., 26, 173 (2014); doi:10.14233/ajchem.2014.15367.
- I.M. Sudarma, A. Kusnandini and M. G. Darmayanti, J. Nat. Prod. (India), 8, 27 (2015).
References
S.A. Burt and R.D. Reinders, Lett. Appl. Microbiol., 36, 162 (2003); doi:10.1046/j.1472-765X.2003.01285.x.
S.I. Kim, J.H. Yi, J.- Tak and Y.-J. Ahn, Vet. Parasitol., 120, 297 (2004); doi:10.1016/j.vetpar.2003.12.016.
Y. Li, C. Xu, Q. Zhang, J.Y. Liu and R.X. Tan, J. Ethnopharmacol., 98, 329 (2005); doi:10.1016/j.jep.2005.01.020.
M. Pisano, G. Pagnan, M. Loi, M.E. Mura, M.G. Tilocca, G. Palmieri, D. Fabbri, M.A. Dettori, G. Delogu, M. Ponzoni and C. Rozzo, Mol. Cancer, 6, 8 (2007); doi:10.1186/1476-4598-6-8.
R. Gao, S. Zhou, P. Zhou and Y. Feng, Asian J. Chem., 26, S173 (2014); doi:10.14233/ajchem.2014.19039.
T. Sumana, P. Iyengar, C. Sanjeevarayappa, K.E. Manoj Kumar and K. Vijay, J. Appl. Chem., 3, 47 (2014).
S.S. Praveen Kumar Darsi, K.S. Nagamani, B. Rama Devi, A. Naidu and P.K. Dubey, Der Pharma Chemica, 3, 35 (2011).
B. Baghernejad, M.M. Heravi, H.A. Oskooie, Y.S. Beheshtiha, G.U. J. Sci., 22, 169 (2009).
D. Gowda, B. Mahesh and G. Shankare, Indian J. Chem., 40B, 75 (2001).
I.M. Sudarma, N. Wazni, N. Wildawaty, E. Yuanita and I.W. Suana, Asian. J. Chem., 26, 173 (2014); doi:10.14233/ajchem.2014.15367.
I.M. Sudarma, A. Kusnandini and M. G. Darmayanti, J. Nat. Prod. (India), 8, 27 (2015).